entacapone
Trade name: comtan
Approved
Oct 19, 1999
Entacapone is a selective, reversible catechol-O-methyl transferase (COMT) inhibitor for the treatment of Parkinson's disease. It is a member of the class of nitrocatechols. When administered concomittantly with levodopa and a decarboxylase inhibitor (e.g., carbidopa), increased and more sustained plasma levodopa concentrations are reached as compared to the administration of levodopa and a decarboxylase inhibitor. The mechanism of action of entacapone is believed to be through its ability to inhibit COMT in peripheral tissues, altering the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to a greater reduction in the manifestations of parkinsonian syndrome. Entacapone is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic Parkinson's Disease who experience the signs and symptoms of end-of-dose "wearing-off". — NCATS
Clinical trial activity
49 trials · 41 clinical orgs · 13 marketing orgs
Earliest trial started Apr 1, 1997 (NCT00262470)
Timeline
1990s
- Jan 1, 1997
Earliest Phase 1 Sponsor(trial)
- Oct 19, 1999
Earliest FDA Approval
- Oct 19, 1999
Orion Corporation — NDA Secondary Org
- Dec 30, 1999
Orion Corporation — First NDA Organization
- Dec 30, 1999
Orion Corporation — NDA Organization
2010s
- May 10, 2012
Sun Pharmaceuticals — Marketing Organization
- Aug 16, 2012
Atlantide Pharmaceuticals — Marketing Organization
- Aug 16, 2012
Wockhardt — Marketing Organization
- May 13, 2013
Mylan — Marketing Organization
- May 13, 2013
PHARMOBEDIENT — Marketing Organization
- Jun 19, 2015
Aurobindo Pharma — Marketing Organization
- Jun 5, 2017
Macleods Pharmaceuticals, Ltd — Marketing Organization
- Jun 5, 2017
Neogen — Marketing Organization
- Aug 31, 2017
Ajanta Pharma Ltd — Marketing Organization
- Oct 3, 2018
Sunshine Lake Pharma Co., Ltd. — Marketing Organization
2020s
- Jan 4, 2022
Alembic — Marketing Organization
- Jan 25, 2022
Rising Pharmaceuticals — Marketing Organization
Indications
Approved for
Studied for
- Autonomic Nervous System Diseases · Phase 1/Phase 2
- Cocaine-Related Disorders · Phase 2/Phase 3
- Healthy Volunteers · Phase 1
- Intestinal Neoplasms · Early Phase 1
- Lewy Body Disease · Phase 1
- Methamphetamine · Early Phase 1
- Multiple System Atrophy · Phase 1/Phase 2
- Obesity · Phase 1/Phase 2
- Orthostatic Intolerance · Phase 1/Phase 2
- Pharmacokinetics · Phase 1
- Pure Autonomic Failure · Phase 1
- Tachycardia · Phase 1/Phase 2
Mechanism of action
- Catechol O-methyltransferaseINHIBITOR
COMT inhibitor
Combination products
Approval history
- approvedOct 19, 1999
Chemistry & pharmacology
SMILES
CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C(=C1)[N+]([O-])=O- Mol. weight
- 305.286 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaEntacapone ↗
- NCATS4975G9NM6T ↗
- ChEMBLCHEMBL953 ↗
Also known as
- 2-cyano-n,n-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide
- comtan
- comtan
- comtan
- comtan
- comtan
- comtess
- comtess
- comtess
- comtess
- (e)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-n,n-diethyl-prop-2-enamide
- (e)-alpha-cyano-n,n-diethyl-3,4-dihydroxy-5-nitrocinnamamide
- (e)-alpha-cyano-n,n-diethyl-3,4-dihydroxy-5-nitrocinnamamide
- entacapona
- entacapona
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacapone
- entacaponum
- entacaponum
- entacom
- levodopa / carbidopa / entacapone
- n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide
- n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide
- novartis brand of entacapone
- or 611
- or-611
- or-611
- or-611
- orion brand of entacapone
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07151378 | Phase 3 | Sep 16, 2025 | University of Tuebingen |
| NCT06180720 | Phase 1 | Dec 20, 2023 | Qingdao University |
| NCT06236230 | Phase 4 | Nov 15, 2023 | Soochow University |
| NCT05976737 | Phase 1 | Aug 17, 2023 | Qingdao University |
| NCT04952194 | Phase 4 | Jan 1, 2022 | Zhejiang University |
| NCT04246437 | Phase 1 | Feb 1, 2020 | Vanderbilt University |
| NCT04006769 | Early Phase 1 (Phase 1) | Jul 31, 2019 | Central South University |
| NCT02764125 | Phase 2 | Apr 1, 2016 | Orion Corporation |
| NCT02554734 | Phase 1 | Aug 1, 2015 | Clinical Research Services Turku, Orion Corporation |
| NCT02448914 | Phase 1 | May 1, 2015 | LobSor Pharmaceuticals AB, TFS Trial Form Support, Uppsala University |
| NCT02452606 | N/A | Mar 1, 2015 | University of Ulsan |
| NCT02349243 | Phase 1/Phase 2 (Phase 2) | Jan 1, 2015 | National Institute of Biological Sciences, Beijing, People's Liberation Army of China, Xijing Hospital |
| NCT01468012 | Phase 2/Phase 3 (Phase 3) | Jul 1, 2014 | Columbia University |
| NCT02058966 | Early Phase 1 (Phase 1) | Jun 1, 2014 | Department of Veteran Affairs, Oregon Health and Science University |
| NCT01840423 | Phase 1 | May 1, 2013 | Orion Corporation, Parexel |
| NCT01688089 | Phase 1 | Sep 1, 2012 | Orion Corporation, Parexel |
| NCT02170376 | Phase 1 | Sep 1, 2011 | Bial |
| NCT01766258 | Phase 2 | May 1, 2011 | Orion Corporation, Paracelsus Elena Klinik Kassel |
| NCT01568073 | Phase 3 | Mar 1, 2011 | Bial |
| NCT01437293 | Phase 1 | Aug 1, 2010 | Columbia University, National Institute on Drug Abuse (NIDA) |
Organizations
Research & Development (41)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Novartis | For profit | 12 | 12 | 4 | 2003 |
| Orion Corporation | For profit | 12 | 11 | 4 | 2002 |
| Bial | For profit | 4 | 4 | 3 | 2005 |
| Columbia University | Academic/Hospital | 2 | 2 | 2 | 2010 |
| Parexel | For profit | 2 | 0 | 1 | 2012 |
| Qingdao University | Academic/Hospital | 2 | 2 | 1 | 2023 |
| Uppsala University | Academic/Hospital | 2 | 1 | 2 | 2008 |
| Vanderbilt University | Academic/Hospital | 2 | 1 | 2 | 1997 |
| Cardiff University | Academic/Hospital | 1 | 0 | 1 | 2005 |
| Central South University | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Cita NeuroPharmaceuticals | For profit | 1 | 0 | 1 | 2006 |
| Clinical Research Services Turku | For profit | 1 | 0 | 1 | 2015 |
| Department of Defense | Government | 1 | 0 | 1 | 2010 |
| Department of Veteran Affairs | Government | 1 | 0 | 1 | 2014 |
| Impax Laboratories | For profit | 1 | 1 | 1 | 2010 |
| INC Research | For profit | 1 | 0 | 1 | 2006 |
| LobSor Pharmaceuticals AB | For profit | 1 | 1 | 1 | 2015 |
| Molecular NeuroImaging | For profit | 1 | 1 | 1 | 2004 |
| National Institute of Biological Sciences, Beijing | Government | 1 | 0 | 1 | 2015 |
| National Institute of Neurological Disorders and Stroke (NINDS) | Government | 1 | 1 | 1 | 2007 |
Marketing (19)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Ajanta Pharma Ltd | For profit | MKTG | Aug 31, 2017 |
| Alembic | For profit | MKTG | Jan 4, 2022 |
| Alembic | For profit | SYN | Jan 4, 2022 |
| Atlantide Pharmaceuticals | For profit | MKTG | Aug 16, 2012 |
| Aurobindo Pharma | For profit | MKTG | Jun 19, 2015 |
| Macleods Pharmaceuticals, Ltd | For profit | MKTG | Jun 5, 2017 |
| Mylan | For profit | MKTG | May 13, 2013 |
| Mylan | For profit | SYN | Aug 13, 2020 |
| Neogen | For profit | MKTG | Jun 5, 2017 |
| Orion Corporation | For profit | NDA | Dec 30, 1999 |
| Orion Corporation | For profit | NDA2 | Oct 19, 1999 |
| PHARMOBEDIENT | For profit | MKTG | May 13, 2013 |
| Rising Pharmaceuticals | For profit | MKTG | Jan 25, 2022 |
| Sun Pharmaceuticals | For profit | MKTG | May 10, 2012 |
| Sun Pharmaceuticals | For profit | SYN | May 10, 2012 |
| Sunshine Lake Pharma Co., Ltd. | For profit | SYN | Oct 3, 2018 |
| Sunshine Lake Pharma Co., Ltd. | For profit | MKTG | Oct 3, 2018 |
| Wockhardt | For profit | MKTG | Aug 16, 2012 |
| Wockhardt | For profit | SYN | Aug 16, 2012 |